Following her college graduation, Weiss began working at Jewish news outlets, including Tablet, Haaretz Newspaper, and The Forward.
She later joined the Wall Street Journal as an op-ed and book review editor in 2013, but she left her post after Donald Trump took office in 2017.
“It was heartbreaking for me to see people who I thought that we sort of shared fundamental values making peace with a candidate who, I mean, just from the most basic perspective ran a campaign on denigrating and demonizing the weakest people in our culture,” she told Reason, explaining she resigned due to the employer’s reluctance to run political opinion pieces deemed “too anti-Trump.”
That same year, Weiss moved to The New York Times‘ opinion desk as a staff editor and writer.
She told the Pittsburgh Jewish Chronicle about the move, “I’ve gone in the last year from being the most progressive person at The Wall Street Journal, to being the most right-wing person at The New York Times.”
In July 2020, she wrote a lengthy resignation letter addressed to publisher A.G. Sulzberger, citing “bullying by colleagues” and an “illiberal environment.”
“The paper of record is, more and more, the record of those living in a distant galaxy, one whose concerns are profoundly removed from the lives of most people,” she wrote, in part. “Nowadays, standing up for principle at the paper does not win plaudits. It puts a target on your back.”
Weiss is also an author. Her first book, How to Fight Anti-Semitism, published in September 2019, won a 2019 National Jewish Book Award and a Natan Notable Book Award.